Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

ABSTRACT

The present invention provides a novel compound that can improve the luminous efficiency, stability and life span of the element, an organic electronic element using the same, and an electronic device thereof.

CROSS-REFERENCE OF RELATED APPLICATIONS

This application is a continuation-in-part of U.S. Pat. Application No.17/756,193 filed on May 19, 2022, which was a 371 of PCT/KR2020/016272filed on Nov. 18, 2020, which claims the benefit of priority from KoreanPatent Application No. 10-2020-0102536 filed on Aug. 14, 2020 and KoreanPatent Application No. 10-2019-0148780 filed on Nov. 19, 2019, thecontents of each of which are incorporated herein by reference in itsentirety.

TECHNICAL FIELD

The present invention relates to compound for organic electronicelement, organic electronic element using the same, and an electronicdevice thereof.

BACKGROUND ART

In general, organic light emitting phenomenon refers to a phenomenonthat converts electric energy into light energy by using an organicmaterial. An organic electronic element using an organic light emittingphenomenon usually has a structure including an anode, a cathode, and anorganic material layer interposed therebetween. Here, in order toincrease the efficiency and stability of the organic electronic element,the organic material layer is often composed of a multi-layeredstructure composed of different materials, and for example, may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

In the organic light emitting diode, the most problematic is thelifetime and the efficiency. As the display becomes large, theefficiency and the lifetime problem must be solved. Efficiency, lifespan, driving voltage and the like are related to each other, as theefficiency is increased, the driving voltage is relatively decreased,and as the driving voltage drops, the crystallization of the organicmaterial due to joule heating generated during driving is reduced, andas a result, the life span tends to increase.

However, simply improving the organic material layer cannot maximize theefficiency. This is because, when the optimal combination of the energylevel and T1 value between each organic material layer and the intrinsicproperties (mobility, interface characteristics, etc.) of the materialare achieved, long life and high efficiency can be achieved at the sametime.

Further, recently, in organic electroluminescent devices, in order tosolve the emission problem in the hole transport layer, anemitting-auxiliary layer must be present between the hole transportlayer and an emitting layer, and it is necessary to develop differentemitting-auxiliary layers according to the respective emitting layers(R, G, B).

In general, electrons are transferred from the electron transport layerto the emitting layer, and holes are transferred from the hole transportlayer to the emitting layer to generate excitons by recombination.

However, the material used for the hole transport layer has a low HOMOvalue and therefore has mostly low T1 value. As a result, the excitongenerated in the emitting layer is transferred to the hole transportlayer, resulting in charge unbalance in the emitting layer, and light isemitted at the interface of the hole transport layer.

When light is emitted at the interface of the hole transport layer, thecolor purity and efficiency of the organic electronic device are loweredand the life span is shortened. Therefore, it is urgently required todevelop an emitting-auxiliary layer having a high T1 value and a HOMOlevel between the HOMO energy level of the hole transport layer and theHOMO energy level of the emitting layer.

Meanwhile, it is necessary to develop a hole injection layer materialhaving stable characteristics, that is, a high glass transitiontemperature, against j oule heating generated when the device is driven,while delaying penetration of the metal oxide from the anode electrode(ITO), which is one of the causes of shortening the lifetime of theorganic electronic device, into the organic layer. The low glasstransition temperature of the hole transport layer material has acharacteristic that when the device is driven, the uniformity of thesurface of the thin film is lowered, which has been reported to have agreat influence on the lifetime of the device. In addition, OLED devicesare mainly formed by a deposition method, and it is necessary to developa material that can withstand long time in deposition, that is, amaterial having high heat resistance characteristics.

That is, in order to sufficiently exhibit the excellent characteristicsof the organic electronic element, a material for forming an organicmaterial layer in an element such as a hole injection material, a holetransport material, a light emitting material, an electron transportmaterial, an electron injection material, an emitting-auxiliary layermaterial should be supported by stable and efficient materials. However,such a stable and efficient organic material layer material for anorganic electronic element has not been sufficiently developed yet.Therefore, development of new materials is continuously required, anddevelopment of materials for the hole transport layer or theemitting-auxiliary layer is urgently required.

DETAILED DESCRIPTION OF THE INVENTION Summary

In order to solve the problems of the background art described above,the present invention has revealed a compound having a novel structure,and that when the compound is applied to an organic electronic element,the luminous efficiency, stability and lifetime of the element aregreatly improved.

Accordingly, it is an object of the present invention to provide a novelcompound, an organic electronic element using the same, and anelectronic device.

Technical Solution

The present invention provides a compound represented by Formula A.

In another aspect, the present invention provides an organic electronicelement comprising the compound represented by Formula A and anelectronic device thereof.

Effects of the Invention

By using the compound according to the present invention, it is possibleto achieve a high luminous efficiency, a low driving voltage, and a highheat resistance of the element, and can greatly improve the color purityand lifespan of the element.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 to FIGS. 2 3 illustrate an example of an organic electronicelement according to the present invention.

FIG. 4 is a graph of measuring capacitance change according to voltageof Comparative Compound A and Compound A-27 of the present invention inan alternating current (AC) driving circuit for OLED according to anembodiment of the present invention.

100, 200, 300: organic electronic element 110 : the first electrode 120: hole injection layer 130 : hole transport layer 140 : emitting layer150 : electron transport layer 160 : electron injection layer 170 :second electrode 180 : light efficiency enhancing Layer 210 : bufferlayer 220 : emitting-auxiliary layer 320 : first hole injection layer330 : first hole transport layer 340 : first emitting layer 350 : firstelectron transport layer 360 : first charge generation layer 361 :second charge generation layer 420 : second hole injection layer 430 :second hole transport layer 440 : second emitting layer 450 : secondelectron transport layer CGL : charge generation layer ST1 : first stackST2 : second stack

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or“connected” to another component, the component may be directlyconnected or connected to the other component, but another component maybe “connected”, “coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxy group” or “aryloxy group”, asused herein, means an oxygen radical attached to an aryl group, but isnot limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has 6 to 60 carbon atoms, but is not limited thereto.Herein, the aryl group or arylene group means a monocyclic andpolycyclic aromatic group, and may also be formed in conjunction with anadjacent group. Examples of “aryl group” may include a phenyl group, abiphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalkenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of monocyclic and polycyclic rings,and may include heteroaliphatic ring and/or heteroaromatic ring. Also,the heterocyclic group may also be formed in conjunction with anadjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring including SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes compound below.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup”, as used herein, means a monovalent or divalent functional group,in which R, R′ and R″ are all hydrogen in the following structures, andthe term “substituted fluorenyl group” or “substituted fluorenylenegroup” means that at least one of the substituents R, R′, R″ is asubstituent other than hydrogen, and include those in which R and R′ arebonded to each other to form a spiro compound together with the carbonto which they are bonded.

The term “spiro compound”, as used herein, has a ‘spiro union’, and aspiro union means a connection in which two rings share only one atom.At this time, atoms shared in the two rings are called ‘spiro atoms’,and these compounds are called ‘monospiro-’, ‘di-spiro-’ and‘tri-spiro-’, respectively, depending on the number of atoms in acompound.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Unless otherwise stated, the term “substituted or unsubstituted”, asused herein, means that substitution is substituted by at least onesubstituent selected from the group consisting of, but is not limitedthereto, deuterium, halogen, an amino group, a nitrile group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylaminegroup, a C₁-C₂₀ alkylthiophen group, a C₆-C₂₀ arylthiophen group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group,a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the presentinvention, as used herein, is applied in the same manner as thesubstituent definition according to the definition of the exponent ofthe following Formula.

wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole substituent R¹ is linked to any oneof the carbon constituting the benzene ring, when a is an integer of 2or 3, each substituent R¹s may be the same and different, when a is aninteger of 4 to 6, and is linked to the benzene ring in a similarmanner, whereas the indication of hydrogen bound to the carbon formingthe benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present inventionand an organic electronic element comprising the same will be described.

The present invention provides a compound represented by Formula A.

wherein, each symbol may be defined as follows.

-   1) Y¹ and Y² are each independently O or S;-   2) L¹ is selected from the group consisting of single bond; a C₆-C₆₀    arylene group; a fluorenylene group; a C₂-C₆₀ heterocyclic group    including at least one heteroatom of O, N, S, Si or P; a fused ring    group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;    -   wherein in case L¹ is an arylene group, it is preferably an        C₆∼C₃₀ arylene group, more preferably an C₆∼C₂₅ arylene group,        such as phenylene, biphenylene, naphthylene, terphenylene, etc.    -   wherein in case L¹ is a fluorenylene group, it may be        9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene,        9,9′-spirobifluorenylene.    -   when L¹ is a heterocyclic group, it is preferably a C₂∼C₃₀        heterocyclic group, and more preferably a C₂∼C₂₄ heterocyclic        group, for example, pyridine, pyrimidine, quinoline,        quinazoline, quinoxaline, dibenzofuran, dibenzothiophene,        naphthobenzothiophene, naphthobenzofuran, benzofuran,        benzothiophene, etc.    -   when L¹ is a fused ring group, it is preferably a fused ring        group of an C₃∼C₃₀ aliphatic ring and an C₆∼C₃₀ aromatic ring,        and more preferably a fused ring group of an C₃∼C₂₄ aliphatic        ring and an C₆∼C₂₄ aromatic ring,-   3) Ar¹ is selected from the group consisting of C₆-C₆₀ aryl group; a    fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one    heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀    aliphatic ring and a C₆-C₆₀ aromatic ring;    -   wherein in case Ar¹ is an aryl group, it is preferably an C₆∼C₃₀        aryl group, more preferably an C₆∼C₂₅ aryl group, such as        phenyl, biphenyl, terphenyl, naphthalene, etc.    -   when Ar¹ is a heterocyclic group, it is preferably a C₂∼C₃₀        heterocyclic group, and more preferably a C₂∼C₂₄ heterocyclic        group, for example, pyrazine, thiophene, pyridine,        pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline,        benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran,        dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine,        phenothiazine, Phenylphenothiazine, etc.    -   when Ar¹ is a fused ring group, it is preferably a fused ring        group of an C₃∼C₃₀ aliphatic ring and an C₆∼C₃₀ aromatic ring,        and more preferably a fused ring group of an C₃∼C₂₄ aliphatic        ring and an C₆∼C₂₄ aromatic ring,-   4) R¹ is selected from the group consisting of a C₆-C₆₀ aryl group;    a fluorenyl group; a C₃-C₆₀ aliphatic cyclic group; a C₂-C₆₀    heterocyclic group including at least one heteroatom of O, N, S, Si    or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀    aromatic ring;    -   wherein in case R¹ is an aryl group, it is preferably an C₆∼C₃₀        aryl group, more preferably an C₆∼C₂₅ aryl group, such as        phenyl, biphenyl, terphenyl, naphthalene, etc.    -   when R¹ is a heterocyclic group, it is preferably a C₂∼C₃₀        heterocyclic group, and more preferably a C₂∼C₂₄ heterocyclic        group, for example, pyrazine, thiophene, pyridine,        pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline,        benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran,        dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine,        phenothiazine, phenylphenothiazine, etc.    -   When R¹ is an aliphatic cyclic group, it may be preferably a        C₃∼C₃₀ aliphatic group, more preferably a C₃∼C₂₄ aliphatic        group.    -   when R¹ is a fused ring group, it is preferably a fused ring        group of an C₃∼C₃₀ aliphatic ring and an C₆∼C₃₀ aromatic ring,        and more preferably a fused ring group of an C₃∼C₂₄ aliphatic        ring and an C₆∼C₂₄ aromatic ring,-   5) R², R³, R⁴, R⁵ and R⁶ are each independently selected from the    group consisting of hydrogen; deuterium; tritium; halogen; cyano    group; nitro group; C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀    heterocyclic group including at least one heteroatom of O, N, S, Si    or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀    aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀    alkynyl group; C₁-C₃₀ alkoxyl group; C₆-C₃₀ aryloxy group; and    -L′-N(R^(a))(R^(b));    -   wherein in case R², R³, R⁴, R⁵ and R⁶ are an aryl group, it is        preferably an C₆∼C₃₀ aryl group, more preferably an C₆∼C₂₅ aryl        group, such as phenyl, biphenyl, terphenyl, naphthalene, etc.    -   wherein in case R², R³, R⁴, R⁵ and R⁶ are a heterocyclic group,        it is preferably a C₂∼C₃₀ heterocyclic group; and more        preferably a C₂∼C₂₄ heterocyclic group, for example, pyrazine,        thiophene, pyridine, pyrimidoindole,        5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline,        benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran,        dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine,        phenothiazine, phenylphenothiazine, etc.    -   wherein in case R², R³, R⁴, R⁵ and R⁶ are a fused ring group, it        is preferably a fused ring group of an C₃∼C₃₀ aliphatic ring and        an C₆∼C₃₀ aromatic ring, more preferably a fused ring group of        an C₃∼C₂₄ aliphatic ring and an C₆∼C₂₄ aromatic ring.    -   wherein in case R², R³, R⁴, R⁵ and R⁶ are an alkyl group, it is        preferably an C₁∼C₃₀ alkyl group, more preferably an C₁∼C₂₄        alkyl group,    -   wherein in case R², R³, R⁴, R⁵ and R⁶ are an alkoxyl group, it        is preferably an C₁∼C₂₄ alkoxyl group,    -   wherein in case R², R³, R⁴, R⁵ and R⁶ are an aryloxy group, it        is preferably an C₆∼C₂₄ aryloxy group,-   6) a, b, c and e are each independently an integer from 0 to 4, d is    an integer from 0 to 3,    -   wherein in case a, b, c and d are 2 or more, R², R³, R⁴, R⁵ and        R⁶ are each in plural being the same or different, and an        adjacent plurality of R² or a plurality of R³ or a plurality of        R⁴ or a plurality of R⁵ or a plurality of R⁶ may be bonded to        each other to form a ring,-   7) L′ is selected from the group consisting of single bond; a C₆-C₆₀    arylene group; a fluorenylene group; a C₃-C₆₀ aliphatic ring; a    C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N,    S, Si or P; and combinations thereof, wherein R^(a) and R^(b) are    each independently selected from the group consisting of a C₆-C₆₀    aryl group; a fluorenyl group; a C₃-C₆₀ aliphatic ring; a C₂-C₆₀    heterocyclic group including at least one heteroatom of O, N, S, Si    or P; and combinations thereof,    -   wherein in case L′ is an arylene group, it is preferably an        C₆∼C₃₀ arylene group, more preferably an C₆∼C₂₅ arylene group,        such as phenylene, biphenylene, naphthylene, terphenylene, etc.    -   wherein in case L′ is a fluorenylene group, it may be        9,9-dimethyl-9H-fluorenylene, 9,9-diphenyl-9H-fluorenylene,        9,9′-spirobifluorenylene.    -   wherein in case L′ is an aliphatic ring, it may be preferably a        C₃-C₃₀ aliphatic ring group, more preferably a C₃-C₂₄ aliphatic        ring group.

In case L′ is a heterocyclic group, it is preferably a C₂∼C₃₀heterocyclic group, and more preferably a C₂∼C₂₄ heterocyclic group, forexample, pyridine, pyrimidine, quinoline, quinazoline, quinoxaline,dibenzofuran, dibenzothiophene, naphthobenzothiophene,naphthobenzofuran, benzofuran, benzothiophene, etc.

-   wherein in case R^(a) and R^(b) are an aryl group, it is preferably    an C₆∼C₃₀ aryl group, more preferably an C₆∼C₂₅ aryl group, such as    phenyl, biphenyl, terphenyl, naphthalene, etc.-   wherein in case R^(a) and R^(b) are a heterocyclic group, it is    preferably a C₂∼C₃₀ heterocyclic group; and more preferably a C₂∼C₂₄    heterocyclic group, for example, pyrazine, thiophene, pyridine,    pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline,    benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran,    dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine,    phenothiazine, phenylphenothiazine, etc.-   wherein in case R^(a) and R^(b) are an aliphatic ring, it may be    preferably a C₃-C₃₀ aliphatic ring group, more preferably a C₃-C₂₄    aliphatic ring group.-   wherein, the aryl group, arylene group, heterocyclic group,    fluorenyl group, fluorenylene group, fused ring group, alkyl group,    alkenyl group, alkoxy group, aryloxy group and aliphatic cyclic    group may be substituted with one or more substituents selected from    the group consisting of deuterium; halogen; silane group; siloxane    group; boron group; germanium group; cyano group; nitro group;    C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group;    C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group;    C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group;    C₂∼C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl    group; C₈-C₂₀ arylalkenyl group; and -L′-N(R_(a))(R_(b)); wherein    the substituents may be bonded to each other to form a saturated or    unsaturated ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic    ring, a C₆-C₆₀ aromatic ring, or a C₂-C₆₀ heterocyclic group, or a    fused ring formed by combination thereof.

Also, Formula A is represented by any one of Formulas A-1 to A-3.

Wherein, Y¹, Y², L¹, Ar¹, R¹, R², R³, R⁴, R⁵, R⁶, a, b, c, d and e arethe same as defined in Formula A.

Also, Formula A is represented by any one of Formulas A-4 to A-7.

Wherein, Y¹, Y², L¹, Ar¹, R¹, R², R³, R⁴, R⁵, R⁶, a, b, c, d and e arethe same as defined in Formula A.

Also, Formula A is represented by Formula A-8.

Wherein, Y¹, Y², L¹, Ar¹, R¹, R², R³, R⁴, R⁵, a, b, c, d, L′, R^(a) andR^(b) are the same as defined in Formula A. R⁷ is the same as thedefinition of R², f is an integer from 0 to 3.

Also, Ar¹ is represented by any one of Formulas Ar-1 to Ar-6.

Wherein, each symbol may be defined as follows.

-   *- indicates the bonding position-   R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are the same or different from each    other and are each independently selected from the group consisting    of hydrogen; deuterium; halogen; cyano group; nitro group; C₆-C₆₀    aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including    at least one heteroatom of O, N, S, Si or P; a fused ring group of a    C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; C₁-C₅₀ alkyl    group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₁-C₃₀ alkoxyl    group; C₆-C₃₀ aryloxy group;-   wherein in case R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are an aryl group,    it is preferably an C₆∼C₃₀ aryl group, more preferably an C₆∼C₂₅    aryl group, such as phenyl, biphenyl, terphenyl, naphthalene, etc.-   wherein in case R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are a heterocyclic    group, it is preferably a C₂∼C₃₀ heterocyclic group; and more    preferably a C₂∼C₂₄ heterocyclic group, for example, pyrazine,    thiophene, pyridine, pyrimidoindole,    5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline,    carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene,    benzothienopyrimidine, benzofuropyrimidine, phenothiazine,    phenylphenothiazine, etc.-   wherein R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are a fused ring group, it    is preferably a fused ring group of an C₃∼C₃₀ aliphatic ring and an    C₆∼C₃₀ aromatic ring, more preferably a fused ring group of an    C₃∼C₂₄ aliphatic ring and an C₆∼C₂₄ aromatic ring.-   wherein in case R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are an alkyl group,    it is preferably an C₁∼C₃₀ alkyl group, more preferably an C₁∼C₂₄    alkyl group,-   wherein in case R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are an alkoxyl    group, it is preferably an C₁∼C₂₄ alkoxyl group,-   wherein in case R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are an aryloxy    group, it is preferably an C₆∼C₂₄ aryloxy group,-   Y is O, S, CR^(x)R^(y) orNR^(z),-   R^(a)′, R^(b)′, R^(x), R^(y) and R^(z) are each independently    selected from the group consisting of a C₆-C₆₀ aryl group; a C₂-C₆₀    heterocyclic group including at least one heteroatom of O, N, S, Si    or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀    aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀    alkynyl group; C₁-C₃₀ alkoxyl group; and C₆-C₃₀ aryloxy group; or    R^(a)′ and R^(b)′ may be bonded to each other to form a ring, or    R^(x) and R^(y) may be bonded to each other to form a ring,-   wherein in case R^(a)′, R^(b)′, R^(x), R^(y) and R^(z) are an aryl    group, it is preferably an C₆∼C₃₀ aryl group, more preferably an    C₆∼C₂₅ aryl group, such as phenyl, biphenyl, terphenyl, naphthalene,    etc.-   wherein in case R^(a)′, R^(b)′, R^(x), R^(y) and R^(z) are a    heterocyclic group, it is preferably a C₂∼C₃₀ heterocyclic group;    and more preferably a C₂∼C₂₄ heterocyclic group, for example,    pyrazine, thiophene, pyridine, pyrimidoindole,    5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline,    carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene,    benzothienopyrimidine, benzofuropyrimidine, phenothiazine,    phenylphenothiazine, etc.-   wherein R^(a)′, R^(b)′, R^(x), R^(y) and R^(z) are a fused ring    group, it is preferably a fused ring group of an C₃∼C₃₀ aliphatic    ring and an C₆∼C₃₀ aromatic ring, more preferably a fused ring group    of an C₃∼C₂₄ aliphatic ring and an C₆∼C₂₄ aromatic ring.-   wherein in case R^(a)′, R^(b)′, R^(x), R^(y) and R^(z) are an alkyl    group, it is preferably an C₁∼C₃₀ alkyl group, more preferably an    C₁∼C₂₄ alkyl group,-   wherein in case R^(a)′, R^(b)′, R^(x), R^(y) and R^(z) are an    alkoxyl group, it is preferably an C₁∼C₂₄ alkoxyl group,-   wherein in case R^(a)′, R^(b)′, R^(x), R^(y) and R^(z) are an    aryloxy group, it is preferably an C₆∼C₂₄ aryloxy group,-   m is an integer from 0 to 5, n, p, q and r are each independently an    integer from 0 to 4, and o is an integer from 0 to 3.

Specifically, the compound represented by Formula A may be any one ofthe following compounds A-1 to A-112, but is not limited thereto.

Also, in another aspect, in the manufacturing process of the organiclight emitting device, the present invention provides a method ofreusing the compound represented by Formula A comprising:

-   the step of depositing an organic light emitting material including    the compound represented by Formula A;-   the step of removing impurities of the crude organic light emitting    material recovered from the deposition apparatus;-   the step of recovering the removed impurities;-   and the step of purifying the recovered impurities to a purity of    99.9% or more;

The step of removing impurities of the crude organic light emittingmaterial recovered from the deposition apparatus may include performinga pre-refining process to obtain a purity of 98% or more byrecrystallization preferably in a recrystallization solvent.

The recrystallization solvent may preferably be a polar solvent having apolarity index (PI) of 5.5 to 7.2.

Preferably, the recrystallization solvent may be used by mixing a polarsolvent having a polarity value of 5.5 to 7.2 and a non-polar solventhaving a polarity value of 2.0 to 4.7.

When the recrystallization solvent is used by mixing a polar solvent anda non-polar solvent, the non-polar solvent may be used in a ratio of 15%(v/v) or less compared to the polar solvent.

Wherein the recrystallization solvent may be used single; or a mixednon-polar solvent; or a mixture of a polar solvent and a non-polarsolvent selected from the group consisting of N-Methylpyrrolidone (NMP)single solvent; or a mixed polar solvent in which any one selected fromthe group consisting of dimethyl imidazolidinone(1,3-Dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide(N,N-dimethyl formamide), dimethyl acetamide and dimethyl sulfoxide ismixed to the methylpyrrolidone; or toluene, Dichloromethane (DCM),Dichloroethane (DCE), Tetrahydrofuran (THF), Chloroform, Ethyl acetateand Butanone.

The preliminary refining process may comprise the step of cooling to 0°C. to 5° C. to precipitate crystals, after dissolving the crude organiclight emitting material recovered from the deposition apparatus in apolar solvent at 90° C. to 120° C.

The preliminary refining process may comprise the step of cooling to 35°C. to 40° C., adding a non-polar solvent, and then cooling to 0° C. to5° C. to precipitate crystals, after dissolving the crude organic lightemitting material recovered from the deposition apparatus in a polarsolvent at 90° C. to 120° C.

The preliminary purification process may comprise the step ofprecipitating crystals while concentrating the solvent and removing thenon-polar solvent, after dissolving the crude organic light emittingmaterial recovered from the deposition apparatus in a non-polar solvent,

The preliminary purification process may comprise the step ofrecrystallization again with a non-polar solvent, afterrecrystallization first with a polar solvent

The step of purifying the recovered impurities to a purity of 99.9% ormore may include the step of performing an adsorption separation processfor adsorbing and removing impurities by adsorbing them to an adsorbent.

The adsorbent may be activated carbon, silica gel, alumina or a materialfor known adsorption applications.

The step of purifying the recovered impurities to a purity of 99.9% ormore may include performing sublimation purification.

Referring to FIG. 1 , the organic electronic element (100) according tothe present invention includes a first electrode (110), a secondelectrode (170), an organic material layer comprising single compoundrepresented by Formula A or 2 or more compounds between the firstelectrode (110) and the second electrode (170), Here, the firstelectrode (110) may be an anode or a positive electrode, and the secondelectrode (170) may be a cathode or a negative electrode. In the case ofan inverted organic electronic element, the first electrode may be acathode, and the second electrode may be an anode.

The organic material layer may sequentially include a hole injectionlayer (120), a hole transport layer (130), an emitting layer (140), anelectron transport layer(150), and an electron injection layer (160)formed in sequence on the first electrode(110). Here, the remaininglayers except the emitting layer (140) may not be formed. The organicmaterial layer may further include a hole blocking layer, an electronblocking layer, an emitting-auxiliary layer (220), a buffer layer (210),etc., and the electron transport layer (150) and the like may serve as ahole blocking layer (see FIG. 2 ).

Also, the organic electronic element according to an embodiment of thepresent invention may further include a protective layer or a lightefficiency enhancing layer (180). The light efficiency enhancing layermay be formed on a surface not in contact with the organic materiallayer among both surfaces of the first electrode or on a surface not incontact with the organic material layer among both surfaces of thesecond electrode. The compound according to an embodiment of the presentinvention applied to the organic material layer may be used as amaterial for a hole injection layer (120), a hole transport layer (130),an emitting-auxiliary layer (220), an electron transport auxiliarylayer, an electron transport layer (150), an electron injection layer(160), a host or dopant of an emitting layer (140) or the lightefficiency enhancing layer. Preferably, for example, the compoundaccording to Formula A of the present invention may be used as amaterial for the emitting-auxiliary layer.

The organic material layer may include 2 or more stacks including a holetransport layer, an emitting layer, and an electron transport layersequentially formed on the anode, and may further include a chargegeneration layer formed between the 2 or more stacks (see FIG. 3 ).

Otherwise, even if the same core is used, the band gap, the electricalcharacteristics, the interface characteristics, and the like may varydepending on which substituent is bonded at which position, thereforethe choice of core and the combination of sub-substituents associatedtherewith is also very important, and in particular, when the optimalcombination of energy levels and T1 values and unique properties ofmaterials(mobility, interfacial characteristics, etc.) of each organicmaterial layer is achieved, a long life span and high efficiency can beachieved at the same time.

The organic electroluminescent device according to an embodiment of thepresent invention may be manufactured using a PVD (physical vapordeposition) method. For example, a metal or a metal oxide havingconductivity or an alloy thereof is deposited on a substrate to form acathode, and the organic material layer including the hole injectionlayer(120), the hole transport layer(130), the emitting layer(140), theelectron transport layer(150), and the electron injection layer(160) isformed thereon, and then depositing a material usable as a cathodethereon can manufacture an organic electroluminescent device accordingto an embodiment of the present invention.

Also, the present invention provides the organic electronic elementwherein the organic material layer is formed by one of a spin coatingprocess, a nozzle printing process, an inkjet printing process, a slotcoating process, a dip coating process or a roll-to-roll process, andthe organic material layer provides an organic electronic elementcomprising the compound as an electron transport material.

As another specific example, the present invention provides an organicelectronic element that is used by mixing the same or differentcompounds of the compound represented by Formula A to the organicmaterial layer.

In another aspect, the present invention provides an emitting-auxiliarylayer composition comprising a compound represented by Formula A, andprovides an organic electronic element comprising the emitting-auxiliarylayer.

Also, the present invention also provides an electronic devicecomprising a display device including the organic electronic element;and a control unit for driving the display device. According to anotheraspect, the present invention provides an display device wherein theorganic electronic element is at least one of an OLED, an organic solarcell, an organic photo conductor, an organic transistor(organic TFT) andan element for monochromic or white illumination. Here, the electronicdevice may be a wired/wireless communication terminal which is currentlyused or will be used in the future, and covers all kinds of electronicdevices including a mobile communication terminal such as a cellularphone, a personal digital assistant(PDA), an electronic dictionary, apoint-to-multipoint(PMP), a remote controller, a navigation unit, a gameplayer, various kinds of TVs, and various kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula Aof the present invention and preparation examples of the organicelectronic element of the present invention will be described in detailby way of example, but are not limited to the following examples.

SYNTHESIS EXAMPLE

The compound (Final product) represented by Formula A according to thepresent invention may be prepared by reacting as in Reaction Scheme 1,but is not limited thereto. (Hal= Br or Cl)

I. Synthesis of Sub 1

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route ofScheme 2, but is not limited thereto. When X¹ is —OH, Sub 1 of ReactionScheme 1 is synthesized by the synthesis route of (1), and when X¹ is—SH, Sub 1 of Reaction Scheme 1 is synthesized by the synthesis route of(2).

1. Synthesis example of Subl-1

Synthesis Example of Sub 1c-1

Sub la-1 (13.0 g, 52.4 mmol), Sub lb-1 (27.6 g, 104.8 mmol),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (23.9 g, 157.3 mmol), pyridine(0.9 mL), Copper powder (0.4 g, 6.8 mmol), CuI (0.5 g, 2.4 mmol) wereplaced in a round flask, DMF (260 mL) was added, and refluxed for 3hours. When the reaction is complete, after cooling to room temperature,3 M HCl is added until the precipitation is complete. Then, theprecipitate was washed with water and dried to obtain 16.8 g (yield:84%) of the product.

Synthesis Example of Sub 1d-1

The obtained Sub 1c-1 (16.8 g, 43.9 mmol) was placed in a round-bottomflask, H₂SO₄ (0.3 mL, 6.1 mmol) was added, and refluxed until all thestarting materials were dissolved. When all the starting materials weredissolved, cool to room temperature, and then add ice water toprecipitate. Thereafter, the precipitate was washed with water, dried,dissolved in CH₂Cl₂, and recrystallized by silicagel column to obtain10.9 g (yield: 68%) of the product.

Synthesis Example of Sub Lf-1

Sub le-1 (7.0 g, 29.9 mmol) was dissolved in THF (100 mL) in around-bottom flask under nitrogen atmosphere, and then cooled to -78° C.After that, n-BuLi (12.1 mL) is slowly titrated and the mixture isstirred for 30 minutes. Then, after dissolving Sub 1d-1(10.9 g, 29.9mmol) obtained in the above synthesis in THF (200 mL), and then slowlytitrate to the reacting round-bottom flask. After stirring for anadditional 1 hour at -78° C., slowly raise to room temperature. When thereaction is complete, the mixture was extracted with ethyl acetate andwater, the organic layer was dried over MgSO₄, concentrated, and theresulting compound was recrystallized by silicagel column to obtain 11.3g (yield: 73%) of the product.

Synthesis Example of Sub 1-1

The obtained Sub lf-1 (11.3 g, 21.8 mmol), acetic acid (52 mL) andconcentrated hydrochloric acid (8.7 mL) were put in a round-bottom flaskand stirred at 60-80° C. under nitrogen atmosphere for 3 hours. When thereaction is complete, the mixture was extracted with CH₂Cl₂ and water,the organic layer was dried over MgSO₄, concentrated, and the resultingcompound was recrystallized by silicagel column to obtain 27.7 g (yield:91%) of the product.

2. Synthesis example of Sub1-6

Synthesis Example of Sub 1c-6

Sub la-1 (20.0 g, 80.6 mmol), Sub lb-6 (22.2 g, 80.6 mmol), Potassiumhydroxide (22.6 g, 403.2 mmol), Copper powder (0.5 g, 8.1 mmol) wereplaced in a round flask, water (400 mL) was added, and refluxed for 12hours. When the reaction is complete, after cooling to room temperature,3 M HC1 is added until the precipitation is complete. Then, theprecipitate was washed with water and dried to obtain 25.1 g (yield:79%) of the product.

Synthesis Example of Sub 1d-6

The obtained Sublc-6 (25.1 g, 63.6 mmol) and H₂SO₄ (0.5 mL) were usedfor the synthesis of Sub 1d-1to obtain 16.7 g (70% yield) of a product.

Synthesis Example of Sub 1f-6

Sub le-1 (10.3 g, 44.3 mmol), n-BuLi (17.9 mL), the obtained Sub ld-6(16.7 g, 44.3 mmol) were used for the synthesis of Sub lf-1 to obtain16.9 g (72% yield) of a product.

Synthesis Example of Sub 1-6

The obtained Sub 1f-6 (16.9 g, 31.8 mmol), acetic acid (75.8 mL) andconcentrated hydrochloric acid (12.7 mL) were used for the synthesis ofSub 1-1 to obtain 13.2 g (yield: 81%) of the product.

3. Synthesis example of Subl-10

Synthesis Example of Sub Lc-10

Sub la-1 (10.0 g, 40.3 mmol), Sub lb-10 (12.2 g, 40.3 mmol), Potassiumhydroxide (11.3 g, 201.6 mmol), Copper powder (0.26 g, 4.0 mmol) wereused for the synthesis of Sub 1c-6 to obtain 13.6 g (yield: 80%) of theproduct.

Synthesis Example of Sub Id-10

The obtained Sub 1c-10 (13.6 g, 32.2 mmol), H₂SO₄ (0.24 mL) were usedfor the synthesis of Sub 1d-1to obtain 8.9 g (yield: 69%) of theproduct.

Synthesis Example of Sub 1f-10

Sub le-1 (5.1 g, 22.0 mmol), n-BuLi (8.9 mL), the obtained Sub 1d-10(8.9 g, 22.0 mmol) were used for the synthesis of Sub lf-1 to obtain 9.2g (yield: 75%) of the product.

Synthesis Example of Sub 1-10

The obtained Sub 1f-10 (9.2 g, 16.5 mmol), acetic acid (39.2 mL), andconcentrated hydrochloric acid (6.6 mL) were used for the synthesis ofSub 1-1 to obtain 7.6 g (yield: 86%) of the product.

4. Synthesis example of Sub 1-20

Synthesis Example of Sub 1c-20

Sub la-1 (15.0 g, 60.5 mmol), Sub 1b-20 (24.8 g, 121.0 mmol),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (27.6 g, 181.4 mmol), pyridine(0.98 mL), Copper powder (0.5 g, 7.9 mmol), CuI (0.5 g, 2.7 mmol) wereused for the synthesis of Sub 1c-1 to obtain 16.1 g (yield: 82%) of theproduct.

Synthesis Example of Sub 1d-20

The obtained Sub 1c-20 (16.1 g, 49.6 mmol) and H₂SO₄ (0.37 mL) were usedfor the synthesis of Sub 1d-1to obtain 10.8 g (yield: 71%) of theproduct.

Synthesis Example of Sub 1f-20

Sub le-1 (8.2 g, 35.2 mmol), n-BuLi (14.2 mL), the obtained Sub 1d-20(10.8 g, 35.2 mmol) were used for the synthesis of Sub lf-1 to obtain12.5 g (yield: 77%) of the product.

Synthesis Example of Sub 1-20

The obtained Sub 1f-20 (12.5 g, 27.1 mmol), acetic acid (64.6 mL), andconcentrated hydrochloric acid (10.8 mL) were used for the synthesis ofSub 1-1 to obtain 10.8 g (yield: 90%) of the product.

5. Synthesis example of Sub 1-33

Synthesis Example of Sub 1c-33

Sub la-1 (13.0 g, 52.4 mmol), Sub 1b-33 (17.1 g, 52.4 mmol), Potassiumhydroxide (14.7 g, 262.1 mmol), Copper powder (0.3 g, 5.2 mmol) wereused for the synthesis of Sub 1c-6 to obtain 19.4 g (yield: 83%) of theproduct.

Synthesis Example of Sub 1d-33

Sub 1c-33 (19.4 g, 43.4 mmol) and H₂SO₄ (0.32 mL) were used for thesynthesis of Sub 1d-1 to obtain 13.4 g (yield: 72%) of the product.

Synthesis Example of Sub 1f-33

Sub le-1 (7.3 g, 31.2 mmol), n-BuLi (12.6 mL), the obtained Sub 1d-33(13.4 g, 31.2 mmol) were used for the synthesis of Sub lf-1 to obtain13.8 g (yield: 76%) of the product.

Synthesis Example of Sub 1-33

The obtained Sub 1f-33 (13.8 g, 23.7 mmol), acetic acid (56.3 mL), andconcentrated hydrochloric acid (9.5 mL) were used for the synthesis ofSub 1-1 to obtain 11.7 g (yield: 88%) of the product.

Meanwhile, the compound belonging to Sub 1 may be a compound as follows,but is not limited thereto, and Table 1 shows FD-MS (FieldDesorption-Mass Spectrometry) values of the compound belonging to Sub 1.

TABLE 1 compound FD-MS compound FD-MS Sub 1-1m/z=500.19(C₃₅H₂₉ClO=501.07) Sub 1-2 m/z=592.20(C₄₁H₃₃ClS=59322) Sub 1-3m/z=536.19(C₃₈H₂₉ClO=537.10) Sub 1-4 m/z=482.14(C₃₄H₂₃ClO=483.01) Sub1-5 m/z=482.14(C₃₄H₂₃ClO=483.01) Sub 1-6 m/z=512.14(C₃₅H₂₅ClS=513.10)Sub 1-7 m/z=460.16(C₃₂H₂₅ClO=461.00) Sub 1-8m/z=448.16(C₃₁H₂₅ClO=448.99) Sub 1-9 m/z=496.16(C₃₅H₂₅ClO=497.03) Sub1-10 m/z=540.17(C₃₇H₂₉ClS=541.15) Sub 1-11 m/z=592.20(C₄₁H₃₃ClS=593.22)Sub 1-12 m/z=524.19(C₃₇H₂₉ClO=525.09) Sub 1-13m/z=576.22(C₄₁H₃₃ClO=577.16) Sub 1-14 m/z=536.19(C₃₈H₂₉ClO=537.10) Sub1-15 m/z=482.14(C₃₄H₂₃ClO=483.01) Sub 1-16 m/z=534.12(C₃₇H₂₃ClS=535.10)Sub 1-17 m/z=492.13(C₃₅H₂₁ClO=493.00) Sub 1-18m/z=518.14(C₃₇H₂₃ClO=519.04) Sub 1-19 m/z=459.08(C₃₀H₁₈ClNS=459.99) Sub1-20 m/z=442.11(C₃ ₁H₁₉ClO=442.94) Sub 1-21 m/z=458.09(C₃₁H₁₉ClS=459.00)Sub 1-22 m/z=534.12(C₃₇H₂₃ClS=535.10) Sub 1-23m/z=568.16(C₄₁H₂₅ClO=569.10) Sub 1-24 m/z=492.13(C₃₅H₂₁ClO=493.00) Sub1-25 m/z=542.14(C₃₉H₂₃ClO=543.06) Sub 1-26 m/z=584.14(C₄₁H₂₅ClS=585.16)Sub 1-27 m/z=568.16(C₄₁H₂₅ClO=569.10) Sub 1-28m/z=540.17(C₃₇H₂₉ClS=541.15) Sub 1-29 m/z=548.10(C₃₇H₂₁ClOS=549.08) Sub1-30 m/z=548.10(C₃₇H₂₁ClOS=549.08) Sub 1-31m/z=532.12(C₃₇H₂₁ClO₂=533.02) Sub 1-32 m/z=532.12(C₃₇H₂₁ClO₂=533.02) Sub1-33 m/z=564.08(C₃₇H₂₁ClS₂=565.14) Sub 1-34m/z=548.10(C₃₇H₂₁ClOS=549.08) Sub 1-35 m/z=559.13(C₃₈H₂₂ClNO₂=560.05)Sub 1-36 m/z=575.11(C₃₈H₂₂ClNOS=576.11) Sub 1-37m/z=574.15(C₄₀H₂₇ClS=575.17) Sub 1-38 m/z=558.18(C₄₀H₂₇ClO=559.11) Sub1-39 m/z=574.15(C₄₀H₂₇ClS=575.17) Sub 1-40 m/z=624.13(C₄₃H₂₅ClOS=625.18)Sub 1-41 m/z=624.13(C₄₃H₂₅ClOS=625.18) Sub 1-42m/z=568.16(C₄₁H₂₅ClO=569.10) Sub 1-43 m/z=498.18(C₃₅H₂₇ClO=499.05) Sub1-44 m/z=463.12(C₃₁H₁₄D₅ClS=464.03) Sub 1-45m/z=539.15(C₃₇H₁₈D₅ClS=540.13) Sub 1-46 m/z=499.17(C₃₅H₁₄D₇ClO=500.04)Sub 1-47 m/z=539.17(C₃₇H₁₄D₇ClO₂=540.07) Sub 1-48m/z=464.14(C₃₁H₂₅ClS=465.05) Sub 1-49 m/z=628.16(C₄₃H₂₁D₄ClOS=629.21)Sub 1-50 m/z=558.18(C₄₀H₂₇ClO=559.11) Sub 1-51m/z=540.17(C₃₇H₂₉ClS=541.15) Sub 1-52 m/z=608.14(C₄₃H₂₅ClS=609.18) Sub1-53 m/z=448.16(C₃₁H₂₅ClO=448.99) Sub 1-54 m/z=476.14(C₃₂H₂₅ClS=477.06)Sub 1-55 m/z=516.17(C₃₅H₂₉ClS=517.13) Sub 1-56m/z=504.22(C₃₅H₃₃ClO=505.10) Sub 1-57 m/z=482.14(C₃₄H₂₃ClO=483.01) Sub1-58 m/z=508.11(C₃₅H₂₁ClS=509.06) Sub 1-59 m/z=447.14(C₃₁H₁₄D₅ClO=447.97) Sub 1-60 m/z=527.20(C₃₇H₁₄D₉ClO=528.09) Sub 1-61m/z=548.10(C₃₇H₂₁ClOS=549.08) Sub 1-62 m/z=548.10(C₃₇H₂₁ClOS=549.08) Sub1-63 m/z=558.18(C₄₀H₂₇ClO=559.11) Sub 1-64 m/z=623.15(C₄₃H₂₆ClNS=624.20)Sub 1-65 m/z=442.11(C₃₁H₁₉ClO=442.94) Sub 1-66m/z=584.14(C₄₁H₂₅ClS=585.16) Sub 1-67 m/z=542.14(C₃₉H₂₃ClO=543.06) Sub1-68 m/z=555.14(C₃₇H₁₄D₇ClOS=556.13) Sub 1-69m/z=508.11(C₃₅H₂₁ClS=509.06) Sub 1-70 m/z=492.13(C₃₅H₂₁ClO=493.00) Sub1-71 m/z=518.14(C₃₇H₂₃ClO=519.04) Sub 1-72 m/z=534.12(C₃₇H₂₃ClS=535.10)

II. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction route ofScheme 2, but is not limited thereto.

(Hal¹ is Br or Cl)

Synthesis examples of specific compounds belonging to Sub 2 are asfollows.

1. Synthesis example of Sub 2-1

Sub 2b-1 (10.0 g, 59.2 mmol), Pd₂(dba)₃ (1.6 g, 1.8 mmol), NaOt—Bu (17.1g, 177.7 mmol), 50 wt% P(t-Bu)₃ (1.4 ml, 3.6 mmol), Toluene (250 ml)were added to Sub 2a-1 (12.0 g, 59.2 mmol) and stirred at 100° C. Whenthe reaction is complete, the mixture was extracted with CH₂Cl₂ andwater, the organic layer was dried over MgSO₄, concentrated, and theresulting compound was recrystallized by silicagel column to obtain 17.6g (yield: 89%) of the product.

2. Synthesis example of Sub 2-29

Sub 2b-29 (9.6 g, 45.7 mmol), Pd₂(dba)₃ (1.3 g, 1.4 mmol), NaOt—Bu (13.2g, 137.2 mmol), 50 wt% P(t-Bu)₃ (1.1 ml, 2.7 mmol), Toluene (230 ml)were added to Sub 2a-29 (10.0 g, 45.7 mmol) and 15.2 g (yield: 85%) ofthe product was obtained by using the synthesis method of Sub 2-1.

3. Synthesis example of Sub 2-72

Sub 2b-72 (5.0 g, 27.0 mmol), Pd₂(dba)₃ (0.7 g, 0.8 mmol), NaOt—Bu (7.8g, 81.1 mmol), 50 wt% P(t-Bu)₃ (0.66 ml, 1.6 mmol), Toluene (230 ml)were added to Sub 2a-72 (10.0 g, 27.0 mmol) and 12.1 g (yield: 87%) ofthe product was obtained by using the synthesis method of Sub 2-1.

Meanwhile, the compound belonging to Sub 2 may be the followingcompounds, but is not limited thereto, and Table 2 shows FD-MS values ofthe compounds belonging to Sub 2.

TABLE 2 compound FD-MS compound FD-MS Sub 2-1 m/z=33 5.13 (C₂₄H₁₇NO=335.41) Sub 2-2 m/z=3 35.13 (C₂₄H₁₇NO=335.41) Sub 2-3 m/z=33 5.13(C₂₄H₁₇NO=33 5.41) Sub 2-4 m/z=401.12(C₂₈H₁₉NS=401.53) Sub 2-5m/z=461.18(C₃₄H₂₃NO=461.56) Sub 2-6 m/z=331.14(C₂₂H₂₁NS=331.48) Sub 2-7m/z=487.19(C₃₆H₂₅NO=487.60) Sub 2-8 m/z=385.15(C₂₈H₁₉NO=385.47) Sub 2-9m/z=401.12(C₂₈H₁₉NS=401.53) Sub 2-10 m/z=375.16(C₂₇H₂₁NO=375.47) Sub2-11 m/z=375.16(C₂₇H₂₁NO=375.47) Sub 2-12 m/z=365.09(C₂₄H₁₅NOS=365.45)Sub 2-13 m/z=365.09(C₂₄H₁₅NOS=365.45) Sub 2-14m/z=451.19(C₃₃H₂₅NO=451.57) Sub 2-15 m/z=349.11(C₂₄H₁₅NO₂=349.39) Sub2-16 m/z=401.12(C₂₈H₁₉NS=401.53) Sub 2-17 m/z=335.13(C₂₄H₁₇NO=335.41)Sub 2-18 m/z=335.13(C₂₄H₁₇NO=335.41) Sub 2-19m/z=375.16(C₂₇H₂₁NO=375.47) Sub 2-20 m/z=391.19(C₂₈H₂₅NO=391.51) Sub2-21 m/z=385.15(C₂₈H₁₉NO=385.47) Sub 2-22 m/z=385.15(C₂₈H₁₉NO=385.47)Sub 2-23 m/z=259.10(C₁₈H₁₃NO=259.31) Sub 2-24m/z=424.16(C₃₀H₂₀N₂O=424.5) Sub 2-25 m/z=335.13(C₂₄H₁₇NO=335.41) Sub2-26 m/z=381.06(C₂₄H₁₅NS₂=381.51) Sub 2-27 m/z=365.09(C₂₄H₁₅NOS=365.45)Sub 2-28 m/z=375.16(C₂₇H₂₁NO=375.47) Sub 2-29m/z=391.14(C₂₇H₂₁NS=391.53) Sub 2-30 m/z=375.16(C₂₇H₂₁NO=375.47) Sub2-31 m/z=411.16(C₃₀H₂₁NO=411.50) Sub 2-32 m/z=351.11(C₂₄H₁₇NS=351.47)Sub 2-33 m/z=335.13(C₂₄H₁₇NO=335.41) Sub 2-34m/z=335.13(C₂₄H₁₇NO=335.41) Sub 2-35 m/z=411.16(C₃₀H₂₁NO=411.50) Sub2-36 m/z=391.14(C₂₇H₂₁NS=391.53) Sub 2-37 m/z=427.14(C₃₀H₂₁NS=427.56)Sub 2-38 m/z=427.14(C₃₀H₂₁NS=427.56) Sub 2-39m/z=451.19(C₃₃H₂₅NO=451.57) Sub 2-40 m/z=309.12(C₂₂H₁₅NO=309.37) Sub2-41 m/z=441.12(C₃₀H₁₉NOS=441.55) Sub 2-42 m/z=499.19(C₃₇H₂₅NO=499.61)Sub 2-43 m/z=427.14(C₃₀H₂₁NS=427.56) Sub 2-44m/z=499.19(C₃₇H₂₅NO=499.61) Sub 2-45 m/z=507.11(C₃₄H₂₁NS₂=507.67) Sub2-46 m/z=515.17(C₃₇H₂₅NS=515.67) Sub 2-47 m/z=487.19(C₃₆H₂₅NO=487.60)Sub 2-48 m/z=497.18(C₃₇H₂₃NO=497.60) Sub 2-49m/z=451.19(C₃₃H₂₅NO=451.57) Sub 2-50 m/z=467.17(C₃₃H₂₅NS=467.63) Sub2-51 m/z=451.19(C₃₃H₂₅NO=451.57) Sub 2-52 m/z=467.17(C₃₃H₂₅NS=467.63)Sub 2-53 m/z=335.13(C₂₄H₁₇NO=335.41) Sub 2-54m/z=441.16(C₃₁H₂₃NS=441.59) Sub 2-55 m/z=335.13(C₂₄H₁₇NO=335.41) Sub2-56 m/z=470.23(C₃₄H₁₄D₉NO=470.62) Sub 2-57 m/z=431.17(C₃₀H₂₅NS=431.60)Sub 2-58 m/z=573.21(C₄₃H₂₇NO=573.69) Sub 2-59m/z=351.11(C₂₄H₁₇NS=351.47) Sub 2-60 m/z=529.15(C₃₇H₂₃NOS=529.66) Sub2-61 m/z=513.17(C₃₇H₂₃NO₂=513.60) Sub 2-62 m/z=549.21(C₄₁H₂₇NO=549.67)Sub 2-63 m/z=513.17(C₃₇H₂₃NO₂=513.60) Sub 2-64m/z=516.18(C₃₆H₂₄N₂O₂=516.60) Sub 2-65 m/z=666.27(C₄₉H₃₄N₂O=666.82) Sub2-66 m/z=666.27(C₄₉H₃₄N₂O=666.82) Sub 2-67 m/z=502.20(C₃₆H₂₆N₂O=502.62)Sub 2-68 m/z=532.16(C₃₆H₂₄N₂OS=532.66) Sub 2-69m/z=542.24(C₃₉H₃₀N₂O=542.68) Sub 2-70 m/z=682.24(C₄₉H₃₄N₂S=682.88) Sub2-71 m/z=442.15(C₃₀H₂₂N₂S=442.58) Sub 2-72 m/z=516.18(C₃₆H₂₄N₂O₂=516.60)Sub 2-73 m/z=548.14(C₃₆H₂₄N₂S₂=548.72) Sub 2-74m/z=566.20(C₄₀H₂₆N₂O₂=566.66) Sub 2-75 m/z=502.20(C₃₆H₂₆N₂O=502.62) Sub2-76 m/z=608.19(C₄₂H₂₈N₂OS=608.76) Sub 2-77 m/z=518.18(C₃₆H₂₆N₂S=518.68)Sub 2-78 m/z=594.21(C₄₂H₃₀N₂S=594.78) Sub 2-79m/z=542.24(C₃₉H₃₀N₂O=542.68) Sub 2-80 m/z=666.27(C₄₉H₃₄N₂O=666.82) Sub2-81 m/z=682.24(C₄₉H₃₄N₂S=682.88) Sub 2-82 m/z=666.27(C₄₉H₃₄N₂O=666.82)Sub 2-83 m/z=664.25(C₄₉H₃₂N₂O=664.81) Sub 2-84m/z=426.17(C₃₀H₂₂N₂O=426.52) Sub 2-85 m/z=594.21(C₄₂H₃₀N₂S=594.78) Sub2-86 m/z=442.15(C₃₀H₂₂N₂S=442.58) Sub 2-87 m/z=578.24(C₄₂H₃₀N₂O=578.72)Sub 2-88 m/z=618.27(C₄₅H₃₄N₂O=618.78) Sub 2-89m/z=682.24(C₄₉H₃₄N₂S=682.88) Sub 2-90 m/z=502.20(C₃₆H₂₆N₂O=502.62) Sub2-91 m/z=664.25(C₄₉H₃₂N₂O=664.81) Sub 2-92 m/z=499.19(C₃₇H₂₅NO=499.61)Sub 2-93 m/z=441.12(C₃₀H₁₉NOS=441.55) Sub 2-94m/z=381.06(C₂₄H₁₅NS₂=381.51) Sub 2-95 m/z=441.12(C₃₀H₁₉NOS=441.55) Sub2-96 m/z=365.09(C₂₄H₁₅NOS=365.45) Sub 2-97 m/z=349.11(C₂₄H₁₅NO₂=349.39)Sub 2-98 m/z=447.17(C₃₀H₂₅NOS=447.60) Sub 2-99m/z=441.12(C₃₀H₁₉NOS=441.55) Sub 2-100 m/z=441.12(C₃₀H₁₉NOS=441.55) Sub2-101 m/z=441.12(C₃₀H₁₉NOS=441.55) Sub 2-102m/z=459.17(C₃₁H₂₅NOS=459.61)

III. Synthesis of Final Product

1. Synthesis example of A-3

After dissolving Sub 1-3 (10 g, 18.6 mmol) with Toluene (250 mL) in around bottom flask, Sub 2-34 (6.2 g, 18.6 mmol), Pd₂(dba)₃ (0.5 g, 0.6mmol), P(t-Bu)₃ (50 wt% Sol.) (0.5 mL, 1.1 mmol), NaOt—Bu (5.8 g, 55.9mmol) were added and stirred at 80° C. when the reaction was complete,the mixture was extracted with CH2Cl₂ and water, the organic layer wasdried over MgSO₄, concentrated, and the resulting compound was purifiedby silicagel column and sublimation to obtain 13.5 g (yield: 87%) of theproduct.

2. Synthesis example of A-6

Sub 1-6 (13 g, 25.3 mmol) and Sub 2-6 (8.4 g, 25.3 mmol), Pd₂(dba)₃ (0.7g, 0.8 mmol), NaOt—Bu (7.3 g, 76.0 mmol), Anhydrous Toluene (270 mL),P(t-Bu)₃ (50 wt% Sol.) (0.6 mL, 1.5 mmol) were used for the synthesis ofA-3 to obtain 18.2 g (yield: 89%) of the product.

3. Synthesis example of A-9

Sub 1-9 (12.0 g, 24.1 mmol) and Sub 2-9 (9.7 g, 24.1 mmol), Pd₂(dba)₃(0.7 g, 0.7 mmol), NaOt—Bu (7.0 g, 72.4 mmol), Anhydrous Toluene (270mL), P(t-Bu)₃ (50 wt% Sol.) (0.6 mL, 1.5 mmol) were used for thesynthesis of A-3 to obtain 17.7 g (yield: 85%) of the product.

4. Synthesis example of A-31

Sub 1-22 (15.0 g, 28.0 mmol) and Sub 2-30 (10.5 g, 28.0 mmol), Pd₂(dba)₃(0.8 g, 0.8 mmol), NaOt—Bu (8.1 g, 84.1 mmol), Anhydrous Toluene (280mL), P(t-Bu)₃ (50 wt% Sol.) (0.7 mL, 1.7 mmol) were used for thesynthesis of A-3 to obtain 20.1 g (yield: 82%) of the product.

5. Synthesis example of A-35

Sub 1-31 (11.0 g, 20.6 mmol) and Sub 2-94 (7.9 g, 20.6 mmol), Pd₂(dba)₃(0.6 g, 0.6 mmol), NaOt—Bu (6.0 g, 61.9 mmol), Anhydrous Toluene (250mL), P(t-Bu)₃ (50 wt% Sol.) (0.5 mL, 1.2 mmol) were used for thesynthesis of A-3 to obtain 14.3 g (yield: 79%) of the product.

6. Synthesis example of A-81

Sub 1-20 (10.0 g, 22.6 mmol) and Sub 2-72 (11.7 g, 22.6 mmol), Pd₂(dba)₃(0.6 g, 0.7 mmol), NaOt—Bu (6.5 g, 67.7 mmol), Anhydrous Toluene (250mL), P(t-Bu)₃ (50 wt% Sol.) (0.5 mL, 1.4 mmol) were used for thesynthesis of A-3 to obtain 16.9 g (yield: 81%) of the product.

Meanwhile, FD-MS values of compounds A-1 to A-112 of the presentinvention prepared according to the above synthesis examples are shownin Table 3.

TABLE 3 compound FD-MS compound FD-MS A-1 m/z=799.35(C₅₉H₄₅NO₂=800.01)A-2 m/z=891.35(C₆₅H₄₉NOS=892.17) A-3 m/z=835.35(C₆₂H₄₅NO₂=836.05) A-4m/z=835.35(C₆₂H₄₅NO₂=836.05) A-5 m/z=907.35(C₆₈H₄₅NO₂=908.11) A-6m/z=807.30(C₅₇H₄₅NS₂=808.11) A-7 m/z=911.38(C₆₈H₄₉NO₂=912.14) A-8m/z=797.33(C₅₉H₄₃NO₂=798.00) A-9 m/z=861.31(C₆₃H₄₃NOS=862.10) A-10m/z=879.35(C₆₄H₄₉NOS=880.16) A-11 m/z=931.38(C₆₈H₅₃NOS=932.24) A-12m/z=863.38(C₆₄H₄₉NO₂=864.10) A-13 m/z=829.30(C₅₉H₄₃NO₂S=830.06) A-14m/z=905.33(C₆₅H₄₇NO₂S=906.16) A-15 m/z=951.41(C₇₁H₅₃NO₂=952.21) A-16m/z=795.28(C₅sH₃₇NO₃=795.94) A-17 m/z=899.27(C₆₅H₄₁NS₂=900.17) A-18m/z=791.28(C₅₉H₃₇NO₂=791.95) A-19 m/z=817.30(C₆₁H₃₉NO₂=817.99) A-20m/z=798.27(C₅₇H₃₈N₂OS=799.00) A-21 m/z=797.33(C₅₉H₄₃NO₂=798.00) A-22m/z=807.26(C₅₉H₃₇NOS=808.01) A-23 m/z=883.29(C₆₅H₄₁NOS=884.11) A-24m/z=791.28(C₅₉H₃₇NO₂=791.95) A-25 m/z=880.31(C₆₅H₄₀N₂O₂=881.05) A-26m/z=841.30(C₆₃H₃₉NO₂=842.01) A-27 m/z=831.28(C₆₁H₃₇NO₃=831.97) A-28m/z=897.27(C₆₅H₃₉NO₂S=898.09) A-29 m/z=781.30(C₅₈H₃₉NO₂=781.95) A-30m/z=797.28(C₅₈H₃₉NOS=798.02) A-31 m/z=873.31(C₆₄H₄₃NOS=874.11) A-32m/z=879.35(C₆₄H₄₉NOS=880.16) A-33 m/z=923.29(C₆₇H₄₁NO₂S=924.13) A-34m/z=863.23(C₆₁H₃₇NOS₂=864.09) A-35 m/z=877.21(C₆₁H₃₅NO₂S₂=878.08) A-36m/z=831.28(C₆₁H₃₇NO₃=831.97) A-37 m/z=939.26(C₆₇H₄₁NOS₂=940.19) A-38m/z=910.31(C₆₄H₃₄D₇NOS₂=911.20) A-39 m/z=898.32(C₆₅H₄₂N₂O₃=899.06) A-40m/z=966.27(C₆₈H₄₂N₂OS₂=967.22) A-41 m/z=965.31(C₇₀H₄₇NS₂=966.27) A-42m/z=963.32(C₇₀H₄₅NO₂S=964.19) A-43 m/z=913.34(C₆₇H₄₇NOS=914.18) A-44m/z=897.27(C₆₅H₃₉NO₂S=898.09) A-45 m/z=847.25(C₆₁H₃₇NO₂S=848.03) A-46m/z=905.33(C₆₈H₄₃NO₂=906.10) A-47 m/z=833.28(C₆₁H₃₉NOS=834.05) A-48m/z=921.31(C₆₈H₄₈NOS=922.16) A-49 m/z=929.22(C₆₅H₃₉NS₃=930.21) A-50m/z=921.31(C₆₈H₄₃NOS=922.16) A-51 m/z=909.31(C₆₇H₄₃NOS=910.15) A-52m/z=919.29(C₆₈H₄₁NOS=920.14) A-53 m/z=863.23(C₆₁H₃₇NOS₂=864.09) A-54m/z=921.31(C₆₈H₄₃NOS=922.16) A-55 m/z=1031.38(C₇₈H₄₉NO₂=1032.25) A-56m/z=919.29(C₆₈H₄₁NOS=920.14) A-57 m/z=913.39(C₆₈H₅₁NO₂=914.16) A-58m/z=894.32(C₆₄H₃₈D₅NS₂=895.21) A-59 m/z=954.37(C₇₀H₄₂D₅NOS=955.24) A-60m/z=930.37(C₆₈H₃₈D₇NOS=931.22) A-61 m/z=838.32(C₆₁H₃₀D₇NO₃=839.01) A-62m/z=869.31(C₆2H₄₇NS₂=870.18) A-63 m/z=927.31(C₆₇H₃₇D₄NO₂S=928.15) A-64m/z=992.43(C₇₄H₄₀D₉NO₂=993.27) A-65 m/z=1003.38(C₇₄H₅₃NOS=1004.30) A-66m/z=855.35(C₆₂H₄₉NOS=856.14) A-67 m/z=979.35(C₇₄H₄₅NO₂=980.18) A-68m/z=923.27(C₆₇H₄₁NS₂=924.19) A-69 m/z=953.33(C₆₉H₄₇NO₂S=954.20) A-70m/z=919.31(C₆₈H₄₁NO₃=920.08) A-71 m/z=961.39(C₇₂H₅ ₁NO₂=962.20) A-72m/z=919.31(C₆₈H₄₁NO₃=920.08) A-73 m/z=928.37(C₆₇H₄₈N₂O₃=929.13) A-74m/z=1106.43(C₈₁H₅₈N₂OS=1107.43) A-75 m/z=1146.46(C₈₄H₆₂N₂OS=114.749)A-76 m/z=970.45(C₇₁H₅₈N₂O₂=971.26) A-77 m/z=960.32(C₆₇H₄₈N₂OS₂=961.25)A-78 m/z=966.42(C₇₁H₅₄N₂O₂=967.23) A-79 m/z=1146.46(C₈₄H₆₂N₂OS=1147.49)A-80 m/z=888.32(C₆₄H₄₄N₂OS=889.13) A-81 m/z=922.32(C₆₇H₄₂N₂O₃=923.08)A-82 m/z=1020.27(C₇₁H₄₄N₂S₃=1021.33) A-83m/z=1028.40(C₇₅H₅₂N₂O₃=1029.25) A-84 m/z=908.34(C₆₇H₄₄N₂O₂=909.10) A-85m/z=1014.33(C₇₃H₄₆N₂O₂S=1015.24) A-86 m/z=1016.33(C₇₃H₄₈N₂S₂=1017.32)A-87 m/z=1005.38(C₇₃H₄₃D₅N₂OS=1006.29) A-88m/z=1033.46(C₇₆H₄₃D₉N₂O₂=1034.32) A-89 m/z=1072.40(C₈₀H₅₂N₂O₂=1073.31)A-90 m/z=1088.38(C₈₀H₅₂N₂OS=1089.37) A-91m/z=1072.40(C₈₀H₅₂N₂O₂=1073.31) A-92 m/z=1086.36(C₈₀H₅₀N₂OS=1087.35)A-93 m/z=938.30(C₆₇H₄₂N₂O₂S=939.14) A-94m/z=1106.34(C₇₉H₅₀N₂OS₂=1107.40) A-95 m/z=964.35(C₇₀H₄₈N₂OS=965.23) A-96m/z=1165.41(C₈₅H₅₅N₃OS=1166.45) A-97 m/z=1024.40(C₇₆H₅₂N₂O₂=1025.26)A-98 m/z=1088.38(C₈₀H₅₂N₂OS=1089.37) A-99 m/z=908.34(C₆₇H₄₄N₂O₂=909.10)A-100 m/z=1086.36(C₈₀H₅₀N₂OS=1087.35) A-101m/z=964.34(C₆₇H₃₂D₁₀N₂OS₂=965.27) A-102 m/z=1106.37(C₈₀H₅₄N₂S₂=1107.45)A-103 m/z=1008.37(C₇₅H₄₈N₂O₂= 1009.22) A-104m/z=1014.33(C₇₃H₄₆N₂O₂S=1015.24) A-105 m/z=913.25(C₆₅H₃₉NOS₂=914.15)A-106 m/z=821.24(C₅₉H₃₅NO₂S=821.99) A-107 m/z=929.22(C₆₅H₃₉NS₃=930.21)A-108 m/z=929.33(C₆₇H₄₇NO₂S=930.18) A-109 m/z=847.25(C₆₁H₃₇NO₂S=848.03)A-110 m/z=847.25(C₆₁H₃₇NO₂S=848.03) A-111 m/z=939.26(C₆₇H₄₁NOS₂=940.19)A-112 m/z=941.33(C₆₈H₄₇NO₂S=924.19)

Evaluation of Manufacture of Organic Electronic Element [Example 1]Green Organic Light Emitting Diode (Emitting Auxiliary Layer)

An organic electroluminescent device was manufactured according to aconventional method using the compound of the present invention as anemitting auxiliary layer material. First, after vacuum deposition of4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,2-TNATA) to a thickness of 60 nm on the ITO layer (anode) formed on theglass substrate to form a hole injection layer,N,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter, NPB) was vacuum-deposited on the hole injection layer to athickness of 60 nm to form a hole transport layer. Then, the compoundA-3 was vacuum-deposited to a thickness of 20 nm on the hole transportlayer to form an emitting auxiliary layer,4,4′-N,N′-dicarbazole-biphenyl (hereinafter, CBP) as a host material andtris(2-phenylpyridine)-iridium (hereinafter, Ir(ppy)3) as a dopantmaterial on the emitting auxiliary layer were doped at a weight ratio of95:5, and then vacuum-deposited to a thickness of 30 nm to form anemitting layer. Then,(1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, BAlq) is vacuum-deposited to a thickness of 10 nm on theemitting layer to form a hole blocking layer, and on the hole blockinglayer, tris-(8-hydroxyquinoline)aluminum (hereinafter, Alq₃) wasvacuum-deposited to a thickness of 40 nm to form an electron transportlayer. Thereafter, LiF, which is an alkali metal halide, was depositedto a thickness of 0.2 nm to form an electron injection layer, and thenAl was deposited to a thickness of 150 nm to form a cathode, therebymanufacturing an organic electroluminescent device.

[Example 2] to [Example 21] Green Organic Light Emitting Diode (EmittingAuxiliary Layer)

An organic light emitting diode was manufactured in the same manner asin Example 1, except that the compound of the present inventiondescribed in Table 4 were used instead of A-3 as the emitting auxiliarylayer material.

[Comparative Example 1] to [Comparative Example 2]

An organic light emitting diode was manufactured in the same manner asin Example 1, Except that the comparative compound 1 or the comparativecompound 2 described in Table 4 were used instead of A-3 as the emittingauxiliary layer material

Electroluminescence (EL) characteristics were measured by PR-650 ofphotoresearch company by applying a forward bias direct current voltageto the organic light emitting diodes prepared according to Examples 1 to21 and Comparative Example 1 to Comparative Example 2 of the presentinvention, T95 life was measured through a life measurement equipmentmanufactured by McScience at a luminance of 5000 cd/m², and themeasurement results are shown in Table 4.

TABLE 4 compound Voltage (V) Current Density (mA/cm²) Brightness (cd/m²₎ Efficiency (cd/A) Lifetime T(95) CIE x y comparative example (1)comparative compound 1 5.9 28.7 5000.0 17.4 86.5 0.34 0.60 comparativeexample (2) comparative compound 2 5.7 24.8 5000.0 20.2 98.3 0.31 0.63example(1) A-3 4.7 10.3 5000.0 48.5 131.5 0.31 0.62 example(2) A-9 4.811.1 5000.0 45.1 130.9 0.33 0.63 example(3) A-10 4.7 10.0 5000.0 50.0133.4 0.33 0.62 example(4) A-13 4.8 9.9 5000.0 50.7 130.5 0.32 0.60example(5) A-27 4.8 9.9 5000.0 50.6 133.8 0.35 0.62 example(6) A-29 4.710.0 5000.0 50.2 134.2 0.32 0.64 example(7) A-36 4.7 11.0 5000.0 45.5132.3 0.35 0.63 example(8) A-37 4.9 9.6 5000.0 52.0 134.0 0.35 0.63example(9) A-38 4.8 10.1 5000.0 49.3 134.6 0.31 0.64 example(l0) A-424.8 10.5 5000.0 47.4 130.1 0.32 0.64 example(11) A-52 4.7 10.3 5000.048.7 133.5 0.31 0.62 example(12) A-54 4.8 10.0 5000.0 50.1 133.6 0.330.60 example(13) A-60 4.8 9.6 5000.0 51.8 132.6 0.32 0.64 example(14)A-72 4.9 10.6 5000.0 47.1 131.3 0.33 0.65 example(15) A-77 4.7 10.15000.0 49.7 132.7 0.31 0.63 example(16) A-80 4.9 9.7 5000.0 51.6 131.00.32 0.62 example(17) A-81 4.8 10.7 5000.0 46.8 130.9 0.32 0.64example(18) A-89 4.8 11.1 5000.0 45.2 131.8 0.33 0.64 example(19) A-984.8 10.4 5000.0 47.9 131.0 0.30 0.63 example(20) A-106 4.7 10.1 5000.049.7 132.8 0.32 0.62 example(21) A-111 4.8 9.6 5000.0 51.9 132.4 0.310.62

As can be seen from the results in Table 4, when a green organic lightemitting device is manufactured by using the material for an organicelectroluminescent device of the present invention as an emittingauxiliary layer material, compared to the case of using ComparativeCompound 1 or Comparative Compound 2, the driving voltage of the organiclight emitting device could be lowered, and efficiency and lifespan weresignificantly improved.

In detail, the comparative compound and the compound of the presentinvention are the same in including a xanthene core and an aminesubstituent, but there is a difference in the presence or absence of asecondary substituent of the xanthene core and a linkage between thexanthene and an amine.

First, when Comparative Compound 1 and Comparative Compound 2 arecompared, it can be seen that Comparative Compound 2 in which asecondary substituent is further substituted at the 4th position of thexanthene core has improved device results than Comparative Compound 1with no substituents attached. These results show that the value of theenergy level (HOMO, LUMO level) is changed according to the presence orabsence of bonding of the secondary substituent and the bondingposition, and the physical properties of the compound are changed,thereby affecting the overall device performance.

Furthermore, Comparative Compound 2 and the compound of the presentinvention are the same in that the secondary substituent is bonded tothe 4th position of the xanthene core, but there is a difference in thepresence or absence of a linking group between the xanthene core and theamine group. In other words, in the case of Comparative Compound 2, anamine group is bonded to the secondary substituted xanthene core througha linking group phenylene, whereas in the compound of the presentinvention, an amine group is substituted by a direct bond, as a result,it can be seen that the element made of the compound of the presentinvention in which an amine group is bonded to the 4-position of thesecondary substituted xanthene core by a direct bond has the bestperformance.

As a result, the amine group is directly bonded to the secondarysubstituted xanthene core, thereby having greater stereoscopicity, as aresult, it is determined that the overall device performance is improvedby adjusting the packing density between materials, even if asubstituent is bonded at the same position, it suggests that thecharacteristics of the device may vary depending on the presence orabsence of a linking group of the substituent.

Additionally, FIG. 4 is a graph measuring the capacitance changeaccording to the voltage of Comparative Compound A and Compound A-27 ofthe present invention in an alternating current (AC) driving circuit forOLED, and through this, it can be seen that a difference occurs in thecapacitance of the compound depending on the presence or absence of asecondary substituent at a specific position of the xanthene core.

Comparative compound A A-27

OLED displays require high device uniformity, but the current suppliedto the pixels of the OLED changes, and the characteristics of the OLEDdevice fluctuate, which causes deterioration of initial panelcharacteristics or image quality problems such as stains andafterimages, thereby causing reliability problems.

For this reason, it is important to increase the stability of theelement, to be able to supply a constant charge according to the changeof the element, and to facilitate the charge transfer at the interfaceof the OLED device.

In general, a capacitor tries to maintain a potential difference of thesame magnitude as the power supply voltage by collecting charges(charging) when the voltage is high and releasing (discharging) thecharges when the voltage is low. The charge/discharge cycle of such acapacitor varies depending on the ratio of the amount of charge storedwhen a voltage is applied, and capacitance indicates the ability tocharge the charge of the capacitor.

The symbol of capacitance is C, and the unit is farad [F], and refers toa quantity representing the ratio of the amount of charge accumulatedwhen a voltage is applied. If the accumulated charge in the capacitor isQ and the applied voltage is V, then a capacitance of 1 F means thatwhen a voltage of 1 V is applied to the capacitor, a charge of 1 C(coulomb) can be accumulated between two parallel plates. Here, thevoltage V and the amount of charge Q are proportional to each other, andas the voltage V increases, the greater the amount of charge Q ischarged. So, when the voltage V is the same, the larger the capacitanceC, the more charge is charged.

That is, the relationship between the voltage, the amount of charge, andthe capacitance is expressed as follows.

Q = C × V

The three physical factors of capacitance are the active area of thecapacitor conductors (plates), the distance between the conductors, andthe dielectric constant of the dielectric medium used between theconductors, and by applying this, the capacitance can be expressed bythe following equation.

$C = \frac{\varepsilon_{r}\varepsilon_{0} \times A}{d}$

ε_(r): relative permittivity (dielectric constant), ε₀ permittivity invacuum, A : electrode plate area, d :distance between two electrodes

An OLED device can be said to be a single capacitor made of amulti-layered organic material (dielectric) between two electrodes, andunlike general capacitors, when more than a certain amount of energy isapplied to the element, the electric charge moves to the internalorganic material layer, and the capacitance changes according to theinternal charge transfer.

In other words, capacitance represents the charge storage capacity of acompound in an OLED device. When the capacitance is large, charges(holes) are continuously accumulated at the interface of the emittingauxiliary layer, and charge injection into the emitting layer isrelatively slow, so that the charge transfer does not occur smoothly.Due to this, charges and electrons meet late in the emitting layer, andas the charge accumulates at the interface of the emitting auxiliarylayer, it is not resolved well, so even if the power supply is stoppeddue to the charge remaining at the interface, a low gray phenomenonoccurs in which current flows. As a result, this phenomenon causes aproblem of deterioration of the image quality of the OLED device panel.Therefore, when a compound with a small capacitance is used in an OLEDdevice, since the charge accumulation time at the interface of theemitting auxiliary layer is shortened and the charge is supplied to theemitting layer smoothly, the low gray phenomenon can be solved and thestability of the OLED device can be improved.

Referring to FIG. 4 , it can be seen that the graph area of the compoundA-27 of the present invention is small compared to the comparativecompound A, which means that the capacitance of the compound A-27 of thepresent invention is smaller. In detail, Section a represents a changein capacitance due to charge (holes) injection from the emittingauxiliary layer to the emitting layer, and Section b is a section inwhich charges meet electrons in the emitting layer to recombine and emitlight.

Comparative Compound A, which does not have a secondary substituent inthe xanthene core, has a large capacitance, so charges are continuouslyaccumulated at the interface or inside the emitting auxiliary layer, sothat the charge injection into the emitting layer is delayed, so thatthe charge transfer is not performed smoothly. For this reason, it canbe seen that the charge and the electron meet late in the emittinglayer, and the charge transfer is not well resolved as the chargeaccumulates at the interface of the emitting auxiliary layer. That is,the organic electronic element using Comparative Compound A, even ifpower supply is stopped due to the charge remaining at the interface,may have a low gray phenomenon in which an afterimage of light remainsmay occur, which may cause deterioration of OLED device characteristicsor image quality problems such as stains and afterimages, resulting inreliability problems.

However, since the capacitance of Compound A-27 of the present inventionis small, it can be seen that the capacitance rapidly decreases inSection b as charges are injected and discharged into the emitting layeras quickly as charges are accumulated at the interface or inside of theemitting auxiliary layer.

As a result, by using a compound in which a secondary substituent isbonded to the xanthene core, charge injection from the emittingauxiliary layer to the emitting layer is smoothly performed, so that thecharge mobility is excellent, and through this, it is shown that thedriving voltage, efficiency, and lifespan of the overall element areimproved as the stability of the OLED device is increased.

In the case of the emitting auxiliary layer, the correlation between thehole transport layer and the emitting layer (host) should be understood,therefore it will be very difficult for a person skilled in the art toinfer the characteristics of the emitting auxiliary layer in which thecompound of the present invention is used even if a similar core isused.

Furthermore, although the element characteristics were described inwhich the compound of the present invention was applied to only onelayer of the emitting auxiliary layer in the evaluation result of theabove-described device fabrication, but it may also be applied to a casein which a hole transport layer or both a hole transport layer and anemitting auxiliary layer are formed using the compound of the presentinvention.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

What is claimed:
 1. A compound represented by Formula A:

wherein: 1) Y¹ and Y² are each independently O or S; 2) L¹ is selectedfrom the group consisting of single bond; a C₆-C₆₀ arylene group; afluorenylene group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; 3) Ar¹ is selected from the groupconsisting of C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; 4) R¹ is selected from the group consisting of a C₆-C₆₀ arylgroup; a fluorenyl group; a C₃-C₆₀ aliphatic cyclic group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; 5) R², R³, R⁴, R⁵ and R⁶ are each independently selected from thegroup consisting of hydrogen; deuterium; tritium; halogen; cyano group;nitro group; C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si or P; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; C₁-C₅₀alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₁-C₃₀ alkoxylgroup; C₆-C₃₀ aryloxy group; and -L′-N(R^(a))(R^(b)); 6) a, b, c and eare each independently an integer from 0 to 4, d is an integer from 0 to3, wherein in case a, b, c and d are 2 or more, R², R³, R⁴, R⁵ and R⁶are each in plural being the same or different, and an adjacentplurality of R² or a plurality of R³ or a plurality of R⁴ or a pluralityof R⁵ or a plurality of R⁶ may be bonded to each other to form a ring,7) L′ is selected from the group consisting of single bond; a C₆-C₆₀arylene group; a fluorenylene group; a C₃-C₆₀ aliphatic ring; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; and combinations thereof, wherein R^(a) and R^(b) are eachindependently selected from the group consisting of a C₆-C₆₀ aryl group;a fluorenyl group; a C₃-C₆₀ aliphatic ring; a C₂-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P; and combinationsthereof, wherein, the aryl group, arylene group, heterocyclic group,fluorenyl group, fluorenylene group, fused ring group, alkyl group,alkenyl group, alkoxy group, aryloxy group and aliphatic cyclic groupmay be substituted with one or more substituents selected from the groupconsisting of deuterium; halogen; silane group; siloxane group; borongroup; germanium group; cyano group; nitro group; C₁-C₂₀ alkylthiogroup; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group;C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substitutedwith deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀cycloalkyl group; C₇-C₂₀ arylalkyl group; C₈-C₂₀ arylalkenyl group; and-L′-N(R_(a))(R_(b)); wherein the substituents may be bonded to eachother to form a saturated or unsaturated ring, wherein the term ‘ring’means a C₃-C₆₀ aliphatic ring, a C₆-C₆₀ aromatic ring, or a C₂-C₆₀heterocyclic group, or a fused ring formed by combination thereof. 2.The compound of claim 1, wherein Formula A is represented by any one ofFormulas A-1 to A-3:

wherein Y¹, Y², L¹, Ar¹, R¹, R², R³, R⁴, R⁵, R⁶, a, b, c, d and e arethe same as defined in claim
 1. 3. The compound of claim 1, whereinFormula A is represented by any one of Formulas A-4 to A-7:

wherein Y¹, Y², L¹, Ar¹, R¹, R², R³, R⁴, R⁵, R⁶, a, b, c, d and e arethe same as defined in claim
 1. 4. The compound of claim 1, whereinFormula A is represented by Formula A-8:

wherein Y¹, Y², L¹, Ar¹, R¹, R², R³, R⁴, R⁵, a, b, c, d, L′, R^(a) andR^(b) are the same as defined in claim
 1. R⁷ is the same as definitionof R² in claim 1, and f is an integer of 0 to
 3. 5. The compound ofclaim 1, wherein Ar¹ is represented by any one of Formulas Ar-1 to Ar-6:

wherein: *- indicates the bonding position, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ andR¹⁶ are the same or different from each other and are each independentlyselected from the group consisting of hydrogen; deuterium; halogen;cyano group; nitro group; C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; C₁-C₅₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group;C₁-C₃₀ alkoxyl group; C₆-C₃₀ aryloxy group; Y is O, S, CR^(x)R^(y) orNR^(z), R^(a)’, R^(b)’, R^(x), R^(y) and R^(z) are each independentlyselected from the group consisting of a C₆-C₆₀ aryl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; C₁-C₅₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group;C₁-C₃₀ alkoxyl group; and C₆-C₃₀ aryloxy group; or R^(a)’ and R^(b)’ maybe bonded to each other to form a ring, or R^(x) and R^(y) may be bondedto each other to form a ring, m is an integer from 0 to 5, n, p, q and rare each independently an integer from 0 to 4, and o is an integer from0 to
 3. 6. The compound of claim 1, wherein the compound represented byFormula A may be any one of the following compounds A-1 to A-112, but isnot limited thereto:

.
 7. An organic electronic element comprising an anode, a cathode, andan organic material layer formed between the anode and the cathode,wherein the organic material layer comprises a single compound or 2 ormore compounds represented by Formula A of claim
 1. 8. The organicelectronic element of claim 7, wherein the organic material layercomprises at least one of a hole injection layer, a hole transportlayer, an emitting auxiliary layer, an emitting layer, an electrontransport auxiliary layer, an electron transport layer, and an electroninjection layer.
 9. The organic electronic element of claim 7, whereinthe organic material layer is an emitting auxiliary layer.
 10. Theorganic electronic element of claim 7, wherein the organic electronicdevice further comprises a light efficiency enhancing layer formed on atleast one surface of the anode and the cathode, the surface beingopposite to the organic material layer.
 11. The organic electronicelement of claim 7, wherein the organic material layer comprises 2 ormore stacks including a hole transport layer, an emitting layer, and anelectron transport layer sequentially formed on the anode.
 12. Theorganic electronic element of claim 11, wherein the organic materiallayer further comprises a charge generation layer formed between the 2or more stacks.
 13. An electronic device comprising a display devicecomprising the organic electronic element of claim 7; and a control unitfor driving the display device.
 14. An electronic device according toclaim 13, wherein the organic electronic element is at least one of anOLED, an organic solar cell, an organic photo conductor(OPC), organictransistor (organic TFT) and an element for monochromic or whiteillumination.
 15. In the manufacturing process of the organic lightemitting device, a method of reusing the compound represented by FormulaA according to claim 1 comprising: the step of depositing an organiclight emitting material including the compound represented by Formula Aof claim 1; the step of removing impurities of the crude organic lightemitting material recovered from the deposition apparatus; the step ofrecovering the removed impurities; and the step of purifying therecovered impurities to a purity of 99.9% or more.